L-tartaric acid salt of a (1R) diastereomer of a 2-azadihydroxybicyclo 2.2.1!heptane compound and the preparation of 2-azabicyclo 2.2.1!heptane compounds

Abstract

A method for the preparation of a lactam compound of formula ##STR1## wherein R' 1 and R" 1 independently are acyl or aroyl, or taken together form an optionally substituted methylene, and G 1 is hydrogen or an amino protecting group, comprising oxidizing a bis O-protected 1R-2-azadihydroxybicyclo- 2.2.1!heptane compound of formula ##STR2## with about 0.1 mol % to about 1 mol % of RuO 2 or hydrate thereof in the presence of about 3 equivalents of an oxidant to form the lactam compound with an enantiomeric excess of greater than or equal to about 95%.

We claim: 
     
       1. A method for the preparation of a lactam compound of formula ##STR22## wherein R' 1  and R" 1  independently are acyl or aroyl, or taken together form an optionally substituted methylene, and G 1  is hydrogen or an amino protecting group, comprising oxidizing a bis O-protected 1R-2-azadihydroxybicyclo- 2.2.1!heptane compound of formula ##STR23## with about 0.1 mol % to about 1 mol % of RuO 2  or hydrate thereof in the presence of about 3 equivalents of an oxidant to form the lactam compound with an enantiomeric excess of greater than or equal to about 95%. 
     
     
       2. The method according to claim 1 wherein RuO 2  is present at about 0.5 mol %. 
     
     
       3. The method according to claim 1 wherein the lactam compound is formed with an enantiomeric excess of greater than or equal to about 99%.